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(2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol

A new tetra­dentate chiral Schiff base ligand, C(16)H(26)N(2)O(2), has been synthesized by the reaction of acetyl­acetone with (1R,2R)-(−)-1,2-diamino­cyclo­hexane. Both of the mol­ecules in the asymmetric unit are of the same chirality (R configuration), since the absolute configuration was determi...

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Detalles Bibliográficos
Autores principales: Li, Xiu-Zhi, Qu, Zhi-Rong
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961254/
https://www.ncbi.nlm.nih.gov/pubmed/21202336
http://dx.doi.org/10.1107/S160053680800977X
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author Li, Xiu-Zhi
Qu, Zhi-Rong
author_facet Li, Xiu-Zhi
Qu, Zhi-Rong
author_sort Li, Xiu-Zhi
collection PubMed
description A new tetra­dentate chiral Schiff base ligand, C(16)H(26)N(2)O(2), has been synthesized by the reaction of acetyl­acetone with (1R,2R)-(−)-1,2-diamino­cyclo­hexane. Both of the mol­ecules in the asymmetric unit are of the same chirality (R configuration), since the absolute configuration was determined by the starting reagent (1R,2R)-(−)-1,2-diamino­cyclo­hexane. The six-membered cyclo­hexane ring is in a chair conformation, and the substituents are equatorial in the most stable conformation (trans-cyclo­hexyl). At the ring substituents, large conjugated —C=N—CH=C—OH systems exist, resulting from the original ketone converted into the enol form. With H atoms excluded, the atoms of each substituent lie in the same plane. The two mol­ecules in the asymmetric unit have almost the same structure, with slight differences in the torsion angles between the substituents and the cyclo­hexane ring; the corresponding N(1)—(C—C—C)(cyclo­hexa­ne) torsion angles are −177.2 (3) and 179.3 (4)° in one mol­ecule and −176.5 (3) and 178.4 (4)° in the other. Two intra­molecular O—H⋯N hydrogen bonds exist in each mol­ecule.
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spelling pubmed-29612542010-12-30 (2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol Li, Xiu-Zhi Qu, Zhi-Rong Acta Crystallogr Sect E Struct Rep Online Organic Papers A new tetra­dentate chiral Schiff base ligand, C(16)H(26)N(2)O(2), has been synthesized by the reaction of acetyl­acetone with (1R,2R)-(−)-1,2-diamino­cyclo­hexane. Both of the mol­ecules in the asymmetric unit are of the same chirality (R configuration), since the absolute configuration was determined by the starting reagent (1R,2R)-(−)-1,2-diamino­cyclo­hexane. The six-membered cyclo­hexane ring is in a chair conformation, and the substituents are equatorial in the most stable conformation (trans-cyclo­hexyl). At the ring substituents, large conjugated —C=N—CH=C—OH systems exist, resulting from the original ketone converted into the enol form. With H atoms excluded, the atoms of each substituent lie in the same plane. The two mol­ecules in the asymmetric unit have almost the same structure, with slight differences in the torsion angles between the substituents and the cyclo­hexane ring; the corresponding N(1)—(C—C—C)(cyclo­hexa­ne) torsion angles are −177.2 (3) and 179.3 (4)° in one mol­ecule and −176.5 (3) and 178.4 (4)° in the other. Two intra­molecular O—H⋯N hydrogen bonds exist in each mol­ecule. International Union of Crystallography 2008-04-16 /pmc/articles/PMC2961254/ /pubmed/21202336 http://dx.doi.org/10.1107/S160053680800977X Text en © Li and Qu 2008 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Li, Xiu-Zhi
Qu, Zhi-Rong
(2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol
title (2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol
title_full (2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol
title_fullStr (2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol
title_full_unstemmed (2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol
title_short (2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol
title_sort (2z,2′z,4e,4′e)-4,4′-(cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961254/
https://www.ncbi.nlm.nih.gov/pubmed/21202336
http://dx.doi.org/10.1107/S160053680800977X
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